Carbon tetrabromide → HCID 59514333, compound

HRID 254559Notes

Reaction equation

HRID 254559 reaction equation
[CH2:1]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[C:11]([CH2:13]O)=[CH:10][CH:9]=[CH:8]2)[CH3:2].C(Br)(Br)(Br)[Br:16].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[Br:16][CH2:13][C:11]1[C:12]2[C:7](=[CH:6][CH:5]=[CH:4][C:3]=2[CH2:1][CH3:2])[CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 59514335HCID 59514335, compound

Product 1

HCID 59514333HCID 59514333, compoundYield 65.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of (8-ethyl-naphthalen-1-yl)-methanol (760 mg) in dichloromethane (15 ml) was cooled to 0° C. and treated with carbon tetrabromide (2.03 g). A solution of triphenylphosphine (1.28 g) in dichloromethane (15 ml) was added dropwise. The reaction mixture was stirred at r.t. overnight, then concentrated. The crude product was purified by column chromatography (silica gel; cyclohexane→cyclohexane/EtOAc 4:1) to give 1-bromomethyl-8-ethyl-naphthalene (670 mg) as light yellow liquid.

Workup

  1. concentrationconcentrated
  2. customThe crude product was purified by column chromatography (silica gel; cyclohexane→cyclohexane/EtOAc 4:1)

Sources & evidence

ORD record
ord-eaf78a6e70104d01b3203cddf4063976
Source dataset
uspto-grants-2011_01
Patent number
US07875645B2

Reaction notes

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